


Pretty boy

by NoSleepingBeauty



Category: IT (Movies - Muschietti)
Genre: Angst with a Happy Ending, Both Eddie and Stan is alive in this, First Kiss, Fix-It, M/M, Richie likes wearing makeup and skirts, Secrets, They are all bestfriends, idk how to tag
Language: English
Status: Completed
Published: 2020-10-04
Updated: 2020-10-04
Packaged: 2021-03-07 23:28:01
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,865
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26815849
Author URL: https://archiveofourown.org/users/NoSleepingBeauty/pseuds/NoSleepingBeauty
Summary: “Boys don’t wear woman clothing or makeup, Richie! Only females and maybe diseased men.” She tells him, a disgusted look on her face.“Diseased men?” He asks her when she removes the cloth from his mouth to rinse and wet it anew.“You know faggots and fairies,” she lowers her voice, “men that like men. Romantically.”Richie was eight when he first wore a skirt. It didnt go so well.
Relationships: Eddie Kaspbrak/Richie Tozier
Kudos: 67





	Pretty boy

**Author's Note:**

> I watched a video of a man in a skirt, fell in love, pictured Richie in a skirt, then wrote this fic. 
> 
> Me a month ago: I will never watch the clown movie! fuck CLOWNS!  
> Me now: *Clown movie on my mind 24/7* I love Richie *Cries*
> 
> Enjoy!

Richie is eight the first time wears a skirt. His parents are out on a date and the babysitter is passed out on the couch with a romcom playing on the tv. He pictures his mother in her flowy dress and her lips painted red as he sneaks into their bedroom.  
Walking over to his mothers’ side of the wardrobe he pulls out one of her white skirts. He holds it in his hands.

“Pretty.” He whispers softly. Staring at the skirt he thinks for a while before he walks over to the bedroom door. The sound of soft voices and loud snores reaches his ears and slowly he closes the door. He takes a deep breath before he walks over to look at himself in the full-length mirror next to his parents’ wardrobe. His heart is pounding as he first puts his left leg into the skirt then his right carefully pulling it up over his hips. The skirt is too big for him, not surprising since it was a skirt designed for a grown adult and not an eight-year-old boy, and the bottom of the skirt is curled up on the floor. With both hands he holds it in place.

Richie looks at himself in the mirror and decides something is missing. As Richie lets go of the skirt it softly falls down to the floor, lightly tickling his legs on the way down. Stepping out of the ring of fabric he walks over to his mother’s vanity table. Next to his mother’s eyeshadow lays a little black tube, her red lipstick. Richie remembers his mother’s smile as his father compliments her. Red lips and white teeth stretched into a gentle smile. He uncaps the tube and holds it up to his face for a second before he leans as far as he can over the table face towards the mirror. Soon his lips too are painted red. It is not as neatly done as his mothers had been, but for a first try he would say it looked like a pretty good job. Smiling to himself one last time in the mirror he turns around and makes his way back over to the skirt. Quickly stepping in and pulling it up. With the skirt once again back on he now takes a good look in the mirror. He does not think he looks as pretty as his mother had done, but something about the soft fabric against his legs and the look of his smile painted the color of his favorite race car just feels good. He spends some time slowly turning in front of the mirror, twisting his body into different poses, smiling over his shoulder like the pretty people in his mother’s magazine.

“Richie,” the babysitter yells from downstairs, “your parents will be back soon.”

Shuffling his way to the door he throws it open. 

“Jessica! Jessica come look!” He makes his way into the hallway and towards the stairs. A blond-haired girl makes her way up the stairs. As she notices Richie, she lets out a gasp. 

“Richie! What are you doing? Take that off!” She yells as she reaches Richie at the top of the stairs. Jessica grabs his shoulder and pushes him towards the bathroom making him let go of his mother’s skirt. He almost trips to the floor but he catches himself last second and stumbles forward. She steers him through the bathroom door over to the sink before she reaches over towards the cabinet to get a cloth. Richie looks at her through the mirror as she turns the sink on wets the cloth before she uses it to roughly rub the lipstick off. 

“Boys don’t wear woman clothing or makeup, Richie! Only females and maybe diseased men.” She tells him, a disgusted look on her face. 

“Diseased men?” He asks her when she removes the cloth from his mouth to rinse and wet it anew. 

“You know faggots and fairies,” she lowers her voice, “men that like men. Romantically.”

Jessica continues to scrub at his face until the last bit of lipstick is gone.

“There is also the type of people who think wearing women’s clothing will make them one, a woman that is.” Jessica says as she rinses the cloth again and Richie watches as pinkish water slowly turns clear. Richie’s lips are still a little red, but that is mostly from all the rubbing. She wrings out the excess water from the cloth before she throws it into the laundry basket behind her. Jessica turns to Richie, grabs his shoulder and bend down so her face is closer to his. 

“You are not a diseased little boy are you Richie?” Richie shakes his head until his neck hurts, tears in his eyes. She pats him on the head, “good!” 

Downstairs a door opens, and two voices calls out we are home! Jessica walks out the door and as she crosses the threshold, she turns to him.

“I’ll clean up the skirt while you go great your parents. I won’t tell them about what happened tonight as long as it doesn’t happen again.” With that she leaves him alone in the bathroom. Richie sprints out into the hallway, down the stairs where he jumps over the last two steps and runs over to his mother. When he reaches her, he burrows his face into her stomach. His parent’s chuckles at him and jokes that he must have missed them a lot while his mother pats him on the head and his father puts a hand on his back. Richie just nods while, pushes his face even further into his mother while trying to not cry. 

That night as he lies in bed, he thinks about the feeling he had, dressed in his mother’s skirt with his lips covered in her lipstick, and buries it far, far into the back of his head. He pictures Jessica and hears the words “diseased” and “faggot” over and over. Never again he thinks as he rolls over onto his stomach and with silent tears rolling down his cheeks, he presses his face into his pillow. 

\---

Richie is thirteen when he is chased out of the arcade by Henry Bowers and his friends. “Faggot” they yell, and Richie sees himself in his head, eight years old and wearing a skirt many sizes too big. He forgets again when he has to run for his life as the Paul Bunyan statue comes to life and tries to kill him. A while later he tries not to think about it as he carves an R + E into the kissing bridge. 

\---

Richie is fifteen and the whole group is hanging in Richie’s room, except for Bev who they have not heard a word from since she moved to live with her Aunt. Stan and Eddie are sitting shoulder to shoulder against the headrest with Richie laying across the bed close to their feet. They have been joking around trying to come up with the best ideas on what they should all dress up as.

“What do you say Eddie Spaghetti, maybe I should dress up as Mrs. K? God knows there would be nothing sexier to dress up as,” Richie lets out a laugh as Eddie slowly turns red with anger.

“What the fuck Richie?! That is so not funny,” Eddie yells as he kicks at Richie. “And don’t call me that dickhead!” The two begin bickering back and forth. Stan rolls his eyes as he takes the comic that he and Eddie had been reading together, scoots away from Eddie and begins reading alone, already used to blocking out the two idiots. 

“T-that is a b-b-bad idea R-Richie.” Richie turns to where Bill is sharing Richie’s bean bag with Mike, they are both reading a book. 

“Have to agree with Bill on this,” Ben says from where he is slowly spinning around in Richie’s chair. 

“And why, my dear Bill, would that be- “Richie is cutoff as Eddie’s foot hit’s him in the stomach. He groans and curls into a ball. The others begin snickering at his pain. “God damnit Eds! But as I was saying why would that be a bad idea?”

Bill does not look up from his book, he just turns a page and replies: “B-because you would look t-terrible in a d-dress.” 

While the other boys voice their agreement and jokes about how Richie in a dress would be possibly the scariest thing that Halloween, Richie feels like someone poured cold water over him. His chest hurts and while deep-down Richie know it was only meant as a joke, the ever-existing fear that they somehow have found out about Richie’s secret gets the better of him. 

“Shut up!” Richie sits up. “Of course, I wouldn’t wear a fucking dress! Are you stupid!”

No one says anything as Richie storms out of the room, surprised over Richie’s reaction. They had all thought he would react by arguing back, saying something like how he would look good in anything and that if anyone in this room could pull of wearing a dress and look good then it obviously would be him. They still don’t say anything when Richie walks back into the room ten minutes later eyes a little red. Richie doesn’t look at anyone as he picks up a comic from the floor and sits down on the opposite side of the room leaning against his wardrobe.

Ben breaks the silence a few minutes later when he asks if they had all done the math homework. The conversation picks up again. He apologizes afterwards, but none of them jokes about wearing a dress again after that.  
Richie is eighteen when he leaves Derry and forgets. 

\---

The next time Richie wear a skirt it is for a comedy sketch. He is thirty-two and does not remember ever having worn a skirt before. The skirt is soft as it slides over his legs and fits perfectly on his hips. When he sees himself in the mirror, he lets out a whistle.

“Looking good Rich,” he hears someone say behind him as he strikes a posing in front of the mirror. His eyes meet the person standing behind him. Maya, his co actor in the sketch and a good friend, looks him up and down. She is dressed in a pair of jeans with a gray turtleneck. On her head is a short black wig and she has drawn on a beard using eyeshadow. As she walks towards him, she holds up a brown bag and says: “let me fix your makeup, we are on in twenty minutes.”

Fifteen minutes later she is done. As they leave the room he takes on last look at himself, a knee length black skirt, red lips and sharp eyeliner, and feels a sting in his chest which he blames on nerves and a little too much fast food before he follows Maya. 

The audience loves their sketch. Richie takes the skirt home and once in a while he will put it on, feel the soft fabric swish against his leg as he walks around his apartment and tries to ignore the whispers he hears in his mind and try to focus about how good it feels. 

\---

Richie is forty when he gets a call, throws up, leaves in the middle of his show and travels to Derry. 

Richie is forty when Pennywise the dancing clown calls him “pretty boy” and mocks him about knowing his secret. At least now he remembers why a part of him is scared whenever he gets prettied up in the safety of his own home. Every time he has felt nervous as he buys a new skirt or as he looks up videos on how to do his eyeshadow, always in incognito mode looking over his shoulder very ten seconds as if someone would be standing behind him ready to catch him in the act.  
Pennywise dies, Eddie almost dies but makes it out a live and Richie cries. 

The next day they get a phone call from Patty Uris telling them that Stan survived. Richie cries again. 

\---

Eddie begins to divorce his wife and moves to LA to live with Richie in his to-big-for-one-person apartment. Richie has to stop wearing makeup and skirts whenever he want, but once in a while Eddie will leave town on a work trip or to work out things revolving his divorce and Richie will carefully pull out a skirt from where he has hidden it at the back of his closet, and just walk around the apartment. 

One day Eddie comes home, and Richie forgets that his nails are painted a soft green color, his thumb a little chipped from where he has been picking on it. They hug in the hallway, holding a little harder and lasting little longer then a normal hug would last before Richie steps back. 

“Nice nail color, it suits you” Eddie is staring at his hands and Richie feels himself freeze. His chest hurts and his hands start shaking. As Eddie walks past him, he claps him on the shoulder and utters a soft “I like it” before he disappears around the corner. Richie looks down on his hands, still shaking, and tries to think that maybe just maybe things will be fine. A voice in the back of his head says no.

Later he sends a selfie of him and Eddie eating dinner in the Losers club group chat. Him holding up a peace sign with Eddie in the background, a grumpy look on his face, mouth full of spaghetti and middle finger pointed to the camera. Bev is the one to notice his green nails and tells him that the next time she is in town they are watching bad movies, getting drunk and doing each other’s nails. It makes the pain in his heart lessen just a little. 

\---

The first time they kiss is one afternoon after having lived together for a little over a year. They are sitting together on a couch during one of their movie nights. Eddie is sitting sideways on the couch with his back against the armrest and feet in Richie’s lap. It was Richie’s turn to pick a movie and if someone were to ask him what the movie was about, he would not be able to tell them. 

“This movie makes no sense! Why do you always pick so god damn stupid movies?” Eddie has spent the past hour complaining about the movie, but never once has he tried to turn it off. Richie on the other hand has spent the past hour with his hand resting on Eddie’s ankle not paying any attention to the movie. 

“Like everyone knows that splitting up is the worst thing you can ever do and yet-“ Richie would pick the most random movies every time it was his time to pick just to see Eddie voice his thoughts. He would be too caught up in his yelling that he wouldn’t notice the fact that Richie would stare at him throughout the entire movie, even if it did end with all his friends believing that Richie had the worst possible taste in movie. Richie loved him. He had loved him when he was thirteen and now 28 years later, he still loved him. Eddie was just so cute sitting there in one of Richie’s “Trashmouth” merch hoodies and Richie so full of love and happiness just wanted very much to kiss him. For over an hour all Richie had been able to think was I want to kiss you. 

“What did you just say” Richie moves his gaze from where he had been staring at Eddie’s mouth to look Eddie in the eyes. Noticing Eddie’s shocked face Richie felt his heart stop for just a second. “Did you just say you wanted to kiss me?”  
Richie feels lightheaded all of a sudden. The thought of I want to kiss you suddenly pushed away by a new thought: Oh god. His whole body was now shaking and suddenly the nausea kicks in. 

“I…” Richie abruptly shoves Eddie’s feet of his lap and stands up. “I have to go!”

Richie makes it three steps before he is stopped. He looks down at where Eddie has grabbed his arm, the place feels like it is on fire. For a second Richie thinks about ripping his arm out of Eddie’s grasp and running to the bathroom to throw up, cry, throw up again and then possibly take a shower, but one look on Eddie’s face stops him from doing so. Eddie is looking anywhere else then Richie’s face, a soft blush on his face. 

“Look Eddie, I- “He begins to say.

“Did you mean it?” Eddie speaks low. So low it is almost a whisper and Richie can barely hear it over the movie playing on the TV. It feels like his heart is going to jump out of his chest. Eddie is looking at him now and for a second Richie sees something cross his face. Hope. 

“I-“ Richie begins to say, in the back of his mind he can hear Jessica yell at him for wearing a skirt, for being a diseased boy, but then he can see the look on Eddie’s face and her voice is shoved away. “I did.”

It is quiet for a second. Richie feels like he cannot breathe, Eddie is smiling up at him before he leans forward and then they kiss. 

A few days later they tell the Losers. After a round of fucking finally and about time, they all give their congratulations. They then they all make plans to meet up in the near future. 

\---

A month later, a week before Richie’s birthday he gets the apartment to himself. Eddie is on a work trip and in a few days the Losers are all spending a week together in LA to celebrate. Richie wakes up around twelve, spends an hour in bed going through social media before he goes to take a shower. As he stands in front of his closet he thinks for a while before he reaches into the back of his wardrobe and pulls out his black skirt and a white t-shirt and makes his way downstairs to get some breakfast. Softly humming he rounds the corner and comes to a stop. Standing around his kitchen counter is the Losers club, even Eddie which should be half across the country in some boring meeting. He feels a little bit of him break as they all turn and looks at him, they look surprised at seeing him standing there, bare foot in his black skirt. His secret is out and the feelings he had when he was eight and Jessica, his babysitter, was screaming at him that only diseased men dresses as a woman, comes rushing back. Richie stands there wishing that the earth would open up and swallow him whole, as he blinks back the tears in his eyes. Beverly is the first to say something.

“What the fuck, Richie?” This is it he thinks. His friends will all yell at him about how disgusting he is. They will all run out of his home, never to return and Eddie will pack his bags and leave. It will all be on the news: Richie “Trashmouth” Tozier likes to dress in feminine clothing and wear makeup. He will lose his fans, the new ones who showed up after he came out as gay and the old ones who stuck by him even when he was pretending to be a straight man who hated his girlfriend. 

“You look so fucking good!” What.

Suddenly his friends are by his side, catcalling and complimenting him. Talking about how long his legs are and how cute he looks. Bev cracks a joke about how Ben will leave her now after having seen him and his long legs. They all laugh, and Stan puts his arms around his shoulder and Bill ruffles his hair. 

“Wait. Wait! You don’t think me, a middle-aged man, wearing a skirt is weird and wrong?” Richie’s voice is almost a whisper, they all go quiet.

“It’s a skirt? Why would you wearing it be something wrong?” It is Mike this time that breaks the quiet. Richie takes a deep breath and looks at his friends’ soft smiles and kind eyes. 

“Who cares if you like wearing a skirt from time to time? You are still our idiot Trashmouth.” Bill says as he bumps his hip into Richie’s. The others laugh as he almost trips. 

“I like wearing makeup too, sometimes.” He blurts out without thinking, but before he even has time to panic, Beverly lets out a happy gasp and starts talking about how she can do his makeup. The boys all have their own thoughts on what they think would look great and the group starts bickering over which colors look best on him. Richie looks over Beverly’s shoulder to Eddie who so far has not said a thing and thinks that maybe Eddie is the only one who is not comfortable with the idea of him liking feminine stuff. Then his eyes meet Eddie’s, and he takes in Eddie’s dilated pupils, the full-face blush and the way Eddie is licking his lips and Richie’s brain goes oh!

The panic he has felt earlier is now gone and in it’s place he feels excitement and the love he has for the people he calls his family. 

The rest of the day is spent in each other’s company. They end up sending Bill, Ben and Eddie to the store to pick up ingredients for dinner, and while they are away Stan sits with his head on Richie’s shoulder while Beverly paints Richie’s nails. Mike is talking about his latest trip to some place in the world showing them pictures on his phone. Richie cries a little but none of them points it out. 

They all try to make dinner together, but it ends in Ben and Mike sending the rest to the living room as they try to save what is supposed to be their dinner. They all sit in a big group on the couch. It is a tight fit, but no one complains. Together they watch a movie, before the people not living in the apartment has to go. They have one last group hug, then make plans to meet up for lunch at a place downtown at one. Richie waves at them one last time before he closes the door. It takes less than ten seconds from the lock is turned to Richie is suddenly pushed up against the door, lips on his and a hand on his thigh underneath the skirt. Eddie pulls away, presses kisses at his neck and whispers about how fucking good Richie looks and how the entire evening has been fucking torture. 

Eddie then takes his hand and pulls him towards the bedroom. Looking at their intertwined hand Richie thinks about how he has not heard the voice in the back of his head telling him he is doing something wrong this entire evening.

**Author's Note:**

> If you liked this fic then please come talk to me on twitter @NoSleep1ngBeaut  
> I need more friends that I can talk about the clown movie to.   
> I am currently sitting on like half a friend because my friend doesnt really care, but she read my fic and she lets me talk about it all I want anyway. She is like the best. 
> 
> But yeah hope you enjoyed.  
> Also I kinda want to write and nsfw fic based on the end, but I dont know how so idk come scream at me if that is something you would like I guess.


End file.
